Macarecurvatin A - Compound Card

Macarecurvatin A

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Macarecurvatin A

Structure
Zoomed Structure
  • Family: Euphorbiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles CC(=CCc1c2O[C@H](c3ccc(c(c3)O)O)[C@H](C(=O)c2c(c(c1O)CC=C(C)C)O)O)C
InChI InChI=1S/C25H28O7/c1-12(2)5-8-15-20(28)16(9-6-13(3)4)25-19(21(15)29)22(30)23(31)24(32-25)14-7-10-17(26)18(27)11-14/h5-7,10-11,23-24,26-29,31H,8-9H2,1-4H3/t23-,24+/m0/s1
InChIKey RGBUXOATBSIOSO-BJKOFHAPSA-N
Formula C25H28O7
HBA 7
HBD 5
MW 440.49
Rotatable Bonds 5
TPSA 127.45
LogP 4.2
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 440.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Macaranga hurifolia Euphorbiaceae Plantae 396461

Showing of synonyms

  • Pagna JI M, Awazi T, et al. (2022). Antibacterial flavonoids from the fruits of Macaranga hurifolia.. Journal of Asian natural products research,2022, 24(11), 1041-1051. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 224.26 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 148.16 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.35
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.12
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.93
Plasma Protein Binding
84.35
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.93
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.56
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.65
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.3
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-42.12
Rat (Acute)
2.35
Rat (Chronic Oral)
3.62
Fathead Minnow
4.96
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
516.34
Hydration Free Energy
-5.23
Log(D) at pH=7.4
2.65
Log(P)
5.26
Log S
-5.01
Log(Vapor Pressure)
-9.4
Melting Point
186.7
pKa Acid
5.69
pKa Basic
6.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9344
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9037
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8849
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8792
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8790
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8519
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8469
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8342
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8324
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8321
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8216
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 5 0.8215
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8203
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8134
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7958
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7953
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7926
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7905
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7843
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7820
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7800
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7737
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7731
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7712
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7710
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7703
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7702
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7646
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7646
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7578
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7568
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7547
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7534
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7528
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7519
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7470
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7433
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7395
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7349
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7341
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7303
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7302
Regucalcin Q64374 RGN_MOUSE Mus musculus 3 0.7297
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7292
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7277
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7245
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7234
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7233
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7228
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7157
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7149
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7147
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7108
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 5 0.7058
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7041
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7036
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7035
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7032
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7030
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7025
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7023
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7023
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7016
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7008

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